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The play chronicles the adult lives of two African-American brothers as they cope with poverty, racism, work, women, and their troubled upbringings. Lincoln lives with Booth, his younger brother, after being thrown out by his wife. Booth reminds Lincoln that his presence was meant to be a temporary arrangement. But Lincoln, who works at an arcade as a whiteface Abraham Lincoln impersonator, is their sole source of income.

While the work is honest, both brothers find it humiliating. Booth repeatedly attempts to persuade Lincoln to return to running games of Three-card Monte. Lincoln had sworn off the hustle after one of his crew had been shot dead, believing he would be next. Idolizing his brother's former glory, Booth aspires to become a Three-card Montecard sharp, frequently practicing the routine in his apartment, although his act is awkward; his own talent lies in shoplifting.

Booth is preoccupied with a woman named Grace whom he tries to impress with shoplifted luxuries. He boasts to his brother about their relationship, but in truth she spurns his advances. Lincoln reveals that his wife Cookie had misread his depression as lack of interest in her, before she threw him out and slept with Booth. In the present, Lincoln is about to be laid off, replaced at his job by a wax model. Booth suggests that Lincoln save his job by vividly acting out Abraham Lincoln's death throes after the customers shoot him with the provided blank—an idea they rehearse before abandoning.

The brothers reflect on their past together: Their parents deserted them as teenagers. Each parent, before leaving with a new lover, left one brother $500 in cash, which they refer to as their "inheritance". Lincoln spent his; Booth saved and hid his, never even opening the stocking that held it.

After losing his job at the arcade, Lincoln returns to Three-card Monte the next day and comes home exuberant. Meanwhile, Booth boasts that Grace has proposed marriage to him. Lincoln suggests that Booth find employment in order to keep Grace, calling his card sharp abilities "double left-handed." Insulted, Booth challenges him to a game of Three-card Monte. Lincoln leads him to believe that he can win, inducing Booth to wager his $500 inheritance on the game before beating him. Laughing, Lincoln explains that the conceit behind Three-card Monte is that the dealer always decides when he wins. Over Booth's protests, he tries to open the stocking containing the inheritance. An agitated Booth reveals that he had shot Grace. Lincoln attempts to return the inheritance, but Booth dares him to open it instead.

As Lincoln cuts the stocking, Booth brings a gun to Lincoln's neck and shoots him. Booth rants at his brother's corpse for mocking him and stealing his inheritance, before crumpling and sobbing over the dead body.

Parks commented on the play: "I think the meaning of the play isn’t just confined to a man's experience... I think it's about what it means to be family and, in the biggest sense, the family of man, what it means to be connected with somebody else." She noted that the play speaks to "who the world thinks you’re going to be, and how you struggle with that."[7]

The play, first produced downtown at the Joseph Papp Public Theater last year, vibrates with the clamor of big ideas, audaciously and exuberantly expressed. Like Invisible Man Ralph Ellison's landmark novel of 1952, Topdog/Underdog considers nothing less than the existential traps of being African-American and male in the United States, the masks that wear the men as well as vice versa. But don't think for a second that Ms. Parks is delivering a lecture or reciting a ponderous poem. Under the bravura direction of George C. Wolfe, a man who understands that showmanship and intellectual substance are not mutually exclusive, 'Topdog/Underdog' is a deeply theatrical experience.[8]

The play won the 2002 Pulitzer Prize for Drama. The Pulitzer committee wrote of the play:

"A darkly comic fable of brotherly love and family identity, Topdog/Underdog tells the story of Lincoln and Booth, two brothers whose names, given to them as a joke, foretell a lifetime of sibling rivalry and resentment. Haunted by their past, the brothers are forced to confront the shattering reality of their future."[9]